(17S,23S)-23,17-epoxy-3beta,28,29-trihydroxy-27-norlanost-8-en-24-one - Compound Card

(17S,23S)-23,17-epoxy-3beta,28,29-trihydroxy-27-norlanost-8-en-24-one

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(17S,23S)-23,17-epoxy-3beta,28,29-trihydroxy-27-norlanost-8-en-24-one

Structure
Zoomed Structure
  • Family: Plantae - Hyacinthaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Nortriterpenoid
Canonical Smiles CCC(=O)[C@@H]1C[C@H]([C@@]2(O1)CC[C@@]1([C@]2(C)CCC2=C1CC[C@@H]1[C@]2(C)CC[C@@H](C1(CO)CO)O)C)C
InChI InChI=1S/C29H46O5/c1-6-21(32)22-15-18(2)29(34-22)14-13-26(4)20-7-8-23-25(3,19(20)9-12-27(26,29)5)11-10-24(33)28(23,16-30)17-31/h18,22-24,30-31,33H,6-17H2,1-5H3/t18-,22+,23-,24+,25-,26+,27+,29+/m1/s1
InChIKey PGCCXLDWXXFVMP-XEJPXPGQSA-N
Formula C29H46O5
HBA 5
HBD 3
MW 474.68
Rotatable Bonds 4
TPSA 86.99
LogP 4.57
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 474.33
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Eucomis zambesiaca Hyacinthaceae Plantae 208122

Showing of synonyms

  • Sihra JK, Thumser AE, et al. (2015). Constituents of Bulbs of three Species of the Hyacinthaceae (Hyacinthoideae): Eucomis vandermerwei, E. zambesiaca and Resnova humifusa. Natural Product Communications, 2015,10 (7), 1207-1209. [View]
Pubchem: 21632990
Nmrshiftdb2: 70081356

No compound-protein relationship available.

Structure

SMILES: O1CCCC12C3C(CC2)C4=C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 474.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.78
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
80.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.62
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.64
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.3
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-247.72
Rat (Acute)
2.95
Rat (Chronic Oral)
2.08
Fathead Minnow
3.77
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
484.93
Hydration Free Energy
-3.17
Log(D) at pH=7.4
3.7
Log(P)
3.87
Log S
-4.68
Log(Vapor Pressure)
-9.63
Melting Point
213.31
pKa Acid
10.47
pKa Basic
6.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7704

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